Ash the Matchmaker: Advanced
by Level X
Summary: Wherein Ash moves to the next level. After setting up May and Drew, Ash decides to step up his game. His next targets are Paul and Dawn, a nearly impossible mission. Unless you're Ash the matchmaker. Ikari, contest, and poke.
1. Chapter 1

**Disclaimer: Pokemon shall never be mine... Sadly... TT_TT**

**Title: **Ash the Matchmaker: Advanced

**Summary: **Wherein Ash moves to the next level. After setting up May and Drew, Ash decides to step up his game. His next targets are Paul and Dawn, a nearly impossible mission. Unless you're Ash the matchmaker.

**Genre:** Humor, romance...

**A/N:** Once again, ANOTHER new story. See, summer is my happy time. It's when all these ideas pop into my brain and I absolutely NEED to write them. This is actually based off a Naruto story I kinda read after accidentally becoming ONE OF THEM, so... Yeah. Enjoy this story!

* * *

It had been a month after Ash had successfully got May and Drew together. They were a happy couple now, yadda yadda. But Ash wasn't focused on their happiness, no, he was going to tackle another subject. A nearly impossible one that would really put his matchmaking abilities to the test. A case known as Paul and Dawn. Of course, he had requested May, Drew, and Misty's help, and the three had gladly agreed, seeing as they too thought Paul and Dawn had eyes only on each other. In fact, their condition had gotten so bad, people could hear their nonstop bickering a mile away. Literally.

So what was Ash going to do? Well, he was obviously going to find some way to get them together. And he knew just the way to do it.

**XxXxX**

"Excuse me sir, here are the tickets you ordered." A pink haired delivery girl stood on Ash's doorstep, holding out a small package containing said tickets.

Ash nodded to the short woman, extending his arm and taking the packet. "Thank you," he said.

"Could you please sign here, sir?" The woman held out a recipt and a pen. Ash mentally sighed. All he wanted to do was eat dinner.

"Of course," he warmly responded, taking the items from her and quickly scrawling his name on the line. He handed the pen and paper back and waved slightly. "Have a great day!"

"You too, sir!" She waved over her back as she walked down his driveway. Ash couldn't help but laugh in glee as he closed the door. Finally! His tickets were here! The week before, he had booked a flight to a few weeks stay at a resort in Johto, near the beaches. He had ordered six tickets, considering the fact that Misty, May, and Drew were going with him. Oh, and the oblivious almost-couple, commonly known as Paul and Dawn.

His plan was simple: give the two a room together and see how things work out. Of course, along the way, he himself would also be doing some minor poking and prodding. Like "accidentally" leaving them in the hot springs together, or having them "act" like a couple to get into places, and other. He could tell. This summer was going to be very fun.

**SoMeTiMe LaTeR**

"And why exactly do you want _me_ to go with you?"

"Because-"

"Pathetic. Ashy boy doesn't have any of his pathetic friends to bring along, so his last resort is me."

"Well-"

"I'm not going. Get someone else to go with you, like that troublesome girl over there."

"H-Hey! My name's DAWN! WHY CAN'T YOU REMEMBER?!"

The raven haired matchmaker sighed and ran a hand through his already messy hair. This particular mission was definitely going to be harder than he thought. It didn't even officially start yet, and already it was this hard.

"Actually, I'd like for both-" He was cut off as the two started arguing again.

"Sorry, what was that, troublesome?"

"DO YOU HAVE A PROBLEM WITH YOUR HEARING OR SOMETHING?! MY NAME IS DAWN! D-A-!"

"Yes, yes, troublesome, I know you can't stand my epic handsomeness, but please do refrain from screaming your love to me everyday. It hurts my eardrums."

"AGH! YOU! ARE! SO! INFURIATING! I'M OUT!"

"WAIT!" Ash suddenly grabbed her arm as she turned to leave the pokemon center. The blunette turned back to glare at him, fire burning in her eyes. Ash shrunk back slightly, afraid of his blue haired friend's wrath.

"You didn't let me finish! I want BOTH of you two to go with us!"

"Us?" Paul interjected into the conversation with a question of his own. Not that he was interested or anything...

"Yeah, us, as in me, Misty, May, and Drew. And of course you two if you agree."

"Where are we going?" Dawn looked excited.

"We're going to a resort near some awesome beaches in Johto."

"There are awesome beaches in Johto?!"

"If you know where to look."

"Really? I'm in!"

"That's awesome!" Ash grinned widely. Paul scoffed and looked away from the happy friends.

"Paul? Are you going to go?" Dawn asked. She still cared about him...

"Hn." He grunted, still looking away.

"C'mon, please..." Ash begged him. If he still refused, then the ravenhead would have bought all those tickets for nothing. And they were _expensive. _

Ash silently turned to Dawn for help. She sighed and turned toward Paul, bringing out the puppy eyes. One look and he'd be hooked, she knew.

"...No."

"WHAT?!" The other two screamed together.

"I said no. You need to get your ears fixed. I'm not going."

"BUT WHY NOT?" Ash whined. He would have to resort to every trick he had in his book.

"Because I don't want to be stuck with you losers for a month."

"Pleassseeeee?" He begged.

"No."

"Pleasssseeeeeeee?"

"No."

"Pretty please with a cherry on top?"

"... If I say yes, will you stop bugging me?"

"YESYESYES I'LL STOP!"

"Fine then. I'll go."

"YAY!"

"Don't both cheer at the same time!"

"Sorry... Well, here are your tickets, meet us in Goldenrod city tomorrow!" Ash threw them the tickets. Paul looked at the times.

"Wait! I AM NOT WAKING UP AT THREE IN THE MORNING TOMORROW!"

Too late. Ash had already left the center to go with Misty to Goldenrod before everyone else so they could arrange some things. Paul sighed and looked over to Dawn. She was staring at him, confusion evident in her eyes. Without a word, Paul tossed her a ticket and walked out of the center.

After he left, Dawn looked down at the slip in her hands... and nearly screamed. "THREE A.M.?! THE FLIGHT LEAVES AT THREE IN THE MORNING?! I CAN NOT WAKE UP THAT EARLY!"

Glares from all corners of the building warned her to lower her voice. She blushed. But seriously! Her dense friend just _had_ to book them a flight that leaves at three in the morning? And even worse, she would be stuck with _Paul_ for the whole way there. A probably sleepy, cranky, snappy Paul. Oh, was this really going to be _fun._

**XxX**

Outside the building, Ash smirked. Oh, this was so much fun. They would be sleepy and stuck on a plane next to each other for at least seven hours! His plan was off to a great start. Now he could only hope it would have a great end.

* * *

**WAAAH I'M SO SORRY FOR ANOTHER NEW STORY TT_TT On the bright side, though, I'm worried sick about something I can not reveal to you people.**

**... Alright. So I actually wrote most of this on my iPod, with the app Google Drive, so when I suddenly lost EVERYTHING, I freaked. No, I'm not kidding, I literally flung my iPod so hard on the ground that it bounced TWICE. TWICE. **

**Anyways, I tried pulling it up on the computer, hoping I was hallucinating and it DIDN'T save with absolutely nothing on it. Well, it did, and I just spent the past hour digging through my memory trying to rewrite as best I could. BUT THE THING IS, I have the WORST feeling ever that I forgot a MAJOR part of this chapter.**

**And I just know I'm going to suddenly remember, then slap myself silly because it was so obvious what I forgot was the BIGGEST part of the story. **

**Anyways, I don't want to bore those who read these things any longer, so I'm gonna go. Follow, favorite, and/or review!**


	2. Tweaking the Rides

_Me: Hey guys, I'm trying out a new format for my A/N's at the top._

_Ash: And at the bottom!_

_Misty: ASH! GET BACK IN THE STORY!_

_Ash: -rolls eyes and sticks tongue out- Yeah, yeah... Whatever..._

_Me: You should probably go. I need to write out your actions! _

_Ash: Yeah, she's such a copycat. And I think Paul and Dawn hate you. You're putting them on hold for so long, they must be really cold by now._

_Me: Oh, shut up, I'll update it when I have more inspiration. And time. NOW SHOO! –shoves Ash back into story-_

* * *

**Last time...**

_His plan was simple: give the two a room together and see how things work out. Of course, along the way, he himself would also be doing some minor poking and prodding._

_"WAIT!" Ash suddenly grabbed her arm as she turned to leave the pokemon center._

_"You didn't let me finish! I want BOTH of you two to go with us!"_

_Ash threw them the tickets. Paul looked at the times._

_"Wait! I AM NOT WAKING UP AT THREE IN THE MORNING TOMORROW!"_

* * *

"Ash, are you sure this is going to work out?"

"Yeah, yeah, of course! Now help me figure out a way to make them both agree to riding in the same car there!"

"Coming, coming..."

Ash and Misty were currently sitting at a table in the pokemon center of Goldenrod city, beginning phase two of Ash's plan. Right now, all they needed was a way to convince Dawn and Paul to ride in the same car to the resort. A small pile of crumpled papers sat beside Ash, all full of plans they just knew wouldn't work.

"Alright, how about this?" Misty slid a piece of paper with the steps of her plan on it toward Ash. The raven haired trainer studied it, going over all possible causes of failure in his head.

"No, no, this wouldn't work. Right here, in this step, you make us act WAY too suspicious. Paul is bound to figure something out." He pointed to said step.

Misty leaned in and focused her eyes on the words Ash's finger was touching. "Hm... Yeah, I guess we _do_ act weirder than usual there..." She sighed and crumpled the paper up, tossing it onto the pile next to her boyfriend.

Ash had already outlined a new plan. Showing it to Misty, he asked, "What about this?"

Misty read the outline, carefully checking for any mistakes. "Hm... I think... I think this might actually work! But how are we going to find that much luggage?"

Ash smirked, an evil one that sent shivers down Misty's spine. "Just trust me."

* * *

A few hours later, Ash, Misty, May, and Drew were all standing in front of three vans, going over the final details of step two of phase one (phase one: force them together.). May and Drew had been informed of how to act, and what to do if anything went wrong. Which, hopefully, nothing did.

Heavy steps approaching the center informed the four of Dawn and Paul's arrival. Eight eyes looked up to see the two with dark bags under their eyes, looking severely annoyed. The strange haired duo stopped in front of the others, scowling. Internally, Ash chuckled.

"Well? What now?" Paul demanded impatiently, tapping his foot on the stone.

Ash tried his best to smile politely at the tired subjects. "Now, we'll be driving the rest of the way there!"

A silmultaneous "WHAT?! NO!" was heard through the streets surrounding them.

"No! I was just stuck with this jerk for seven hours, I don't need to drive anywhere with him!"

"I don't want to drive this troublesome girl _anywhere_ after that plane ride!"

"Can't we just stay _here_ instead?!"

"Quit your whining, annoying girl..."

"Meanie! Don't make me drive him anywhere! Please!"

"I think you're wrong, troublesome, it'll be _me_ driving _your_ annoying butt there."

"WELL-"

"GUYS!" The arguing almost-couple stopped insulting each other and turned toward Ash. "We really need to go. I know that you two don't want to drive together, but you're going to have to. Both my van and May's are too full to take anyone else, so you two will have to share a car.

"NO!"

"Why can't I just go with May?!"

Ash held back a smirk. "May and Drew won't separate, no matter what we say or do. Misty and I need to be in the same car because we're the only ones who know the way there. I know the easiest route there, but in case you get lost, there's map in the glove compartment." He looked toward Dawn and Paul, but they seemed too lost in their own thoughts to care about what he was saying. Fine with him.

He clapped his hands. "Alright! We all understand, correct?" Without waiting for an answer, he continued. "Yes! Good, let's get moving! We need to make it there before midnight."

With that, he climbed into a van with Misty while May and Drew showed Paul and Dawn their car. The two argued a little before Paul jumped into the driver's side, and Dawn reluctantly slid into the passenger's seat. May and Drew then got into their van, and gave Ash and Misty a thumbs up. Ash smirked. Step two was a success. Next, step three: purposely get them lost.

* * *

_Paul: Well, wasn't that short?_

_Me: Oh shut up. I just needed to get this out of way so I can work on Locked._

_Drew: Yeah, you probably should update that... I'm getting really bored being put on hold!_

_Me: I WILL! I'M SORRY! SORRY! SO SORRY! WHY CAN'T I JUST UPDATE EVERY TWO WEEKS OR SO LIKE NORMAL PEOPLE?! WHY?!_

_Paul: Simple. You're not normal._

_Me: SHUT UP! –pushes Paul back into room 65-_


	3. Getting Lost

**PEOPLE YOU KNOW NOT HOW SORRY I AM FOR UPDATING SO LATE I AM SO SORRY I JUST CAN'T CATCH UP TO LIFE!**

* * *

Ash smirked. Step two was a success.

**XxXxX**

"Ok then, lets go!" Ash shouted out the window before driving away, intending for the others to follow him. May gave a thumbs up to Paul and Dawn, then drove off and followed Ash out of the city.

Dawn looked at Paul. "Well, what are you waiting for?! Drive!"

Paul growled under his breath. "Troublesome brat," he muttered as he pulled out of the lot, glaring out the windshield as he went. "Now gimme that map. I need to know where we're going." Dawn shook her head.

"Nope, you can't read it while driving," she pressed it to her chest. "I'll read it for you."

"Well, you'd better be good at it because we've LOST THE OTHERS!" Paul wasn't doing very well holding back his temper.

"We wouldn't have lost them if you had just hurried up and driven!" Dawn retaliated.

Paul glared over at her and decided not to argue pointlessly with her anymore, instead glancing quickly over at the map in her hands to confirm the next turn.

He turned.

"PAUL, YOU IDIOT! What are you doing, going right?! It was supposed to be a left turn!" Dawn screeched angrily at the purple haired man.

"No, it was a right, the map said so."

"We'll that's because YOU WERE READING IT UPSIDE DOWN!"

"Because you were holding it upside down."

"BECAUSE I NEEDED TO KEEP IT AWAY FROM YOU!"

"... Whatever. Do you have any idea where we are?"

His blue haired passenger squinted at the map in confusion, then shook her head. "Sorry, I have no idea."

"Honestly, of all people..."

"What was that?" Dawn didn't hear him, luckily.

"Nothing, I'll just pull up at some store or something and ask."

"A STORE?! WE'RE ON THE HIGHWAY, YOU CAN'T JUST PULL UP AT SOME STORE!"

"Fine then, I'll get off at the nearest exit."

"You'd better." Dawn responded, crossing her arms. The rest of the drive to the exit was silence, the awkward kind, Paul drove, his eyes glued to the road, and Dawn tried to resist staring at him. They were both really tired and cranky due to the plane ride, and now the car situation really didn't help one bit.

Finally, Paul spotted an exit along the road and quickly made his way to it, speeding down the narrow lane and finding himself in some rundown, old town. Luckily for them, though, that rundown, old town had many shops, most of them open. Dawn grinned widely at the sight of the town, her eyes taking in as many of the various clothes shops as possible.

"Paul! Paul! Can we go there?" She pointed out the window, her excited breath fogging the glass up.

Paul grunted, not bothering to look out the window. "No."

"But why not?" Dawn whined back at him, hoping he'd crack.

"Because I don't want to waste anymore time."

"But shopping isn't wasting time! Aww, come on, please? Please? Please?" Dawn begged.

Paul finally relented, if only to shut the annoying teen up. "Fine. But only of you shut up."

"YAY!"

Paul immediately regretted his decision. Why had he caved? He didn't even like the girl, didn't even want to be around her. So why, when she begged him mercilessly, had he given in? It must have been the air. Always the air.

Dawn didn't know why she did it. As Paul cruised toward the store, thoughts flooded her head. Why did she ask? She wasn't even sure what the store sold, much less if she would actually like it. Maybe it was because she wanted to spend more time with him. No, it couldn't be. She didn't like him, she tried to convince herself. It didn't work so well.

The blue haired girl was jolted out of her thoughts by the feeling of the car roughly stopping in front of the rather crowded store.

"We're here. Now hurry up and get whatever you want, because I just want to get out of here." Paul said to her as he slammed the car door. Dawn nodded eagerly and lead the way in, suddenly excited again.

They went in. The two looked around.

"Oh, no..."

"YES!"

* * *

**I am so sorry for the disappointing chapter, I just needed to get SOMETHING up... Oh well next chappie is the shopping time!**

**Well. I don't know what to say. I'm truly really sorry for being dead for the past few months, but life was eating me whole.**

**I AM SO SORRY FROM NOW ON I PROMISE TO WORK ON MY FANFICS ALL THE TIME SCREW MY SOCIAL LIFE WHO NEEDS THAT.**


End file.
